Tag: M.W:100-200

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2075-45-8, name is 4-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 2075-45-8

Preparation 45 4-Bromo-1-trityl-1H-pyrazole Trityl chloride (9.02 g) was added to a stirred solution of 4-bromopyrazole (4.24 g) and 4-dimethylaminopyridine (0.711 g) in pyridine (90 ml). The reaction mixture was heated to 85 C. for 20 hrs, cooled to room temperature and partitioned between diethyl ether and water. The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. The crude product was recrystallized from hexane/toluene (5/1, 180 ml) to afford the title compound (4.0 g). The remaining solids and the mother liquors were combined and purified by column chromatography on silica gel eluding with pentane/ether (30/1, v/v) to afford a second batch of title compound (3.0 g). deltaH (300 MHz, CDCl3): 7.60 (1H, s), 7.40 (1H, s), 7.30 (9H, m), 7.20 (6H, m).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Pfizer Inc.; US6200978; (2001); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3112-31-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3112-31-0 name is 1H-Pyrazole-3,5-dicarboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of pyrazole-3,5-dicarboxylic acid (75 g, 431 mmol) in 11 of anhydrous methanol was treated with anhydrous HCl gas. The HCl addition was continued for 30 min after which, the solution was allowed to cool to room temperature and allowed to stand for 16 h. The solution was then heated at reflux for 3 h then cooled and the solvent removed at reduced pressure. The resulting white solid was treated with 600 ml of saturated NaHCO3 and extracted into CH2 Cl2 (3*500 ml). The pooled extracts were dried (Na2 SO4), filtered and evaporated at reduced pressure. The resulting white solid was recrystallized from methanol with the addition of anhydrous ether to give dimethyl pyrazole-3,5-dicarboxylate (3-1a). 1 H NMR (CDCl3) delta 7.38 (s, 1H); 3.98 (s, 3H); 3.93 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-3,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5821241; (1998); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of tert-butyl {4-methyl-2-[2-(trifluoromethyl)benzyl]-1,3-thiazol-5-yl}carbamate (400 mg, 1.07 mmol) obtained in Example 209-D) in ethanol (10 mL) was added dropwise concentrated hydrochloric acid (4.8 mL) at room temperature, and the mixture was stirred at 50C for 1.5 hr. The reaction mixture was cooled to room temperature, neutralized with 8M aqueous sodium hydroxide solution, adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in DMA (10 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (161 mg, 1.28 mmol), HATU (487 mg, 1.28 mmol) and DIEA (0.0884 mL, 0.535 mmol) were added at room temperature. The reaction mixture was stirred at 80C overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (13:7-7:13)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (7:3-1:1)], and crystallized from ethyl acetate-hexane to give the title compound (107 mg) as white crystals (yield 26%). MS (ESI+): [M+H]+ 381. 1H NMR (300 MHz, DMSO-d6) delta 2.30 (3H, s), 4.03 (3H, s), 4.39 (2H, s), 7.05 (1H, d, J = 2.3 Hz), 7.51-7.62 (3H, m), 7.69 (1H, d, J = 7.5 Hz), 7.71-7.83 (1H, m), 10.50 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-40-7, These common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1: Synthesis of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 4-Nitropyrazole-3-carboxylic acid (20.0 g, 127.4 mmol) was suspended in CH2Cl2/DMF (99:1, 400 mL), treated cautiously with oxalyl chloride (11.6 mL, 134 mmol) and then stirred at room temperature for 16 h. The reaction mixture was evaporated then re-evaporated with toluene (*3) to give a yellow solid. The resultant acid chloride was suspended in dioxane (400 mL), treated with triethylamine (26.4 mL, 190 mmol) followed by 4-amino-1-BOC-piperidine (25.0 g, 125 mmol) and stirred at room temperature for 6 h. The reaction mixture was filtered and the solid collected stirred in water (500 mL) and then re-filtered. The solid collected was dried in vacuo, azeotroping with toluene, to give the title compound (37.6 g).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/21420; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57012-20-1, name is (1,3-Dimethyl-1H-pyrazol-5-yl)methanol, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 57012-20-1, Quality Control of (1,3-Dimethyl-1H-pyrazol-5-yl)methanol

To a stirring solution of (2,5-dimethyl-2H-pyrazol-3-yl)-methanol (100 mg, 0.79 mmol) in diethyl ether (3 ml.) is added PBr3 (25 //L, 0.26 mmol). The reaction is stirred at room temperature for 18 hours, then water is added. The diethyl ether layer is separated and stored over solid NaOH and used in Step 71b without further characterization.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (1,3-Dimethyl-1H-pyrazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/68418; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 288148-34-5, These common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 4-(5-fluoro-lH-indol-3-yl)-iV’-(4-piperazin-l-ylphenyl)pyrimidin-2-amine (20 mg, 0.051 mmol) in dimethylforamide (1 mL), were added l-methyl-lH-pyrazole-4-sulfonyl chloride (9.3 mg, 0.051 mmol), triethylamine (31.3 mg, 0.309 mmol), and 4-dimethylamino pyridine (cat.). The solution was allowed to stir for 12 hr. After completion of the reaction, the reaction mixture was concentrated and purified by reverse phase chromatography (100% H2O to 100% MeCN) to afford ^(S-fluoro-lH-indol-S-y^-N^-f^tCl-methyl-lH-pyrazoM- yl)sulfonyl]piperazin-l-yl}phenyl)pyrimidin-2-amine as a mono trifluoroacetic acid salt. LRMS m/z (M+H) Calcd: 533.2, found: 533.1.

The synthetic route of 288148-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/149427; (2007); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 478968-48-8 as follows. HPLC of Formula: C7H10N2O3

Step 4. Ethyl 3-methoxy-l-pyrimidin-2-yl-lH-pyrazole-4-carboxylate; Sodium hydride (60% in mineral oil, 528 mg, 13.2 mmol) is added portion wise to a solution of ethyl 3-methoxy-lH-pyrazole-4-carboxylate (1.5 g, 8.81 mmol) in 40 mL of THF at RT. Evolution of H2 (g) is observed. After about 5-10 min, 2-chloropyrirnidine (1.0 g, 8.81 mmol) is added, and the resulting reaction mixture is stirred at reflux for 15 h. After cooling to RT, the reaction is quenched with 10 mL of sat. NH4Cl and 10 mL of water and extracted with CH2Cl2 (2 x 40 mL). The combined organic extracts are dried (Na2SO4), filtered, and evaporated in vacuo to give a brown solid. Purification by silica gel column chromatography (gradient from 50% EtOAc/hexane to EtOAc) affords the title compound as a fluffy white solid.

According to the analysis of related databases, 478968-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2009/12482; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3469-69-0, name is 4-Iodopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3469-69-0

4-Iodo-l-(4-methoxybenzyl)-lH-pyrazole According to Scheme 9 Step 1 : A suspension of 4-iodo-lH-pyrazole (26.3 mmol, 5.11 g), l-(chloromethyl)-4-methoxybenzene (29.0 mmol, 3.95 mL) and K2CO3 (39.5 mmol, 5.46 g) in acetonitrile (150 mL) was heated at 6O0C overnight. The reaction mixture was cooled to room temperature and was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM as eluent to afford 4-iodo-l-(4-methoxybenzyl)-lH-pyrazole (23.2 mmol, 7.3 g, 88%) as a yellow solid. UPLC-MS: RT = 1.02 min; MS m/z ES+= 315.

According to the analysis of related databases, 3469-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA S.A.; BOLEA, Christelle; WO2010/79239; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 852443-61-9, name is 3-(Trifluoromethyl)-1H-pyrazol-5-amine, molecular formula is C4H4F3N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 3-(Trifluoromethyl)-1H-pyrazol-5-amine

Tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l-carboxylate (1.0 g, ca. 2.77 mmol), 3- (trifluoromethyl)-lH-pyrazol-5 -amine (0.28 g, 1.85 mmol) and potassium phosphate (0.79 g, 3.70 mmol) were suspended in 1 -methoxy-2-propanol (10 ml) in a 20 ml microwave vial. The vial was capped and the mixture was heated in a microwave to 180C for 15 min. After cooling to RT, the solvent was evaporated and the residue was treated with water and ethyl acetate. After separation of the layers the aqueous phase was neutralized by addition of HQ 4N and extracted with ethyl acetate. The collected organic layers were dried over magnesium sulfate, filtered and evaporated. The crude product was purified by preparative HPLC (Method 1A). The combined product fractions were neutralized with a 33% ammonia solution and then acetonitrile was evaporated. The aqueous phase was extracted with ethyl acetate and the collected organic fractions were dried over sodium sulfate, filtered and evaporated under vacuo to yield the title compound (132 mg, 19% of theory). LC-MS (Method IB): Rt = 1.06 min, MS (ESIPos): m/z = 387 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 852443-61-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H15N3O2

To a solution of 2-(3-bromophenyl)acetic acid (0.5g, 2.32mmol) in DCM (20mL) was added EDCI (0.88g, 0.4.65mmol) at 0 C followed by DIPEA (1.l2mL, 6.97mmol) and finally added tert-butyl 3-amino-5-methyl- 1 H-pyrazole- 1 -carboxylate (0.4g, 2.O9mmol). The reaction mass was stined for 12h at room temperature. The reaction mixture was quenched with ice-water and diluted with DCM. The aqueous layer was separated and extracted with ethyl acetate (2x25mL). The combined organic phase was washed with brine, dried over Na2504, filtered and concentrated under reduced pressure and purified by eluting with 20% ethyl acetate-hexane in combiflash to afford the title compound (0.3g, 60%). LCMS: mlz = 395.9 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 578008-32-9.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; PODDUTOORI, Ramulu; PANDIT, Chetan; MUKHERJEE, Subhendu; GOSWAMI, Rajeev; (126 pag.)WO2016/193939; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics